Glucopyranosylidene-Spiro-Thiazolinones: Synthetic Studies and Determination of Absolute Configuration by TDDFT-ECD Calculations

Reactions of O-peracylated C-(1-bromo-β-d-glucopyranosyl)formamides with thioamides furnished the corresponding glucopyranosylidene-spiro-thiazolin-4-one. While O-debenzoylations under a variety of conditions resulted in decomposition, during O-deacetylations the addition of MeOH to the thiazolinone moiety was observed, and with EtOH and water similar adducts were isolated or detected. The structure and stereochemistry of the new compounds were established by means of NMR and electronic circular dichroism (ECD) data supported by time-dependent density functional theory ECD (TDDFT-ECD) calculations. TDDFT-ECD calculations could efficiently distinguish the proposed epimeric products having different absolute configuration in the spiro heterocyclic ring

TDDFT-ECD and DFT-NMR studies of thaigranatins A–E and granatumin L isolated from Xylocarpus granatum

TDDFT-ECD calculations were utilized to explain the mirror image or different ECD spectra of previously reported homochiral natural products thaigranatins A–E and granatumin L, the simple comparison of which would result in a wrong stereochemical conclusion. The configurational assignment was confirmed independently and geometrical parameters of the chromophores governing the ECD spectra were identified in the structurally related natural products by analyzing the ECD spectra and geometries of the low-energy computed conformers obtained by different methods. Different conformations of the furan-2-yl-d-lactone subunit were found responsible for the mirror image ECD spectra of the homochiral thaigranatins C–E. Two DFT 13C NMR chemical shift calculation methods and DP4+ analysis were performed on the C-6 epimers of thaigranatin D, which together with the ECD calculation, could determine the absolute configuration of C-6 as (R)

Collision-induced dissociation of aflatoxins

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Varioloid A, a new indolyl-6,10b-dihydro-5aH-[1]benzofuro[2,3-b]indole derivative from the marine alga-derived endophytic fungus Paecilomyces varotii EN-291

A new indolyl-6,10b-dihydro-5aH-[1]benzofuro[2,3-b]indole derivative, varioloid A (1), was isolated from the marine alga-derived endophytic fungus Paecilomyces variotii EN-291. Its structure was elucidated on the basis of extensive analysis of 1D and 2D NMR data and the absolute configuration was determined by time-dependent density functional theory-electronic circular dichroism (TDDFT-ECD) calculations. A similar compound, whose planar structure was previously described but the relative and absolute configurations and 13C NMR data were not reported, was also identified and was tentatively named as varioloid B (2). Both compounds 1 and 2 exhibited cytotoxicity against A549, HCT116, and HepG2 cell lines, with IC50 values ranging from 2.6 to 8.2 µg/mL

Screening of Luzula species native to the Carpathian Basin for anti-inflammatory activity and bioactivity-guided isolation of compounds from Luzula luzuloides (Lam.) Dandy & Wilmott

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Inducing secondary metabolite production by the endophytic fungus Chaetomium sp. through fungal-bacterial co-culture and epigenetic modification

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